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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Our top choices for Osprey condo rentals

Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is AED 421
AED 2,125 total
includes taxes & fees
19 May - 20 May
Chadwick Cove Resort & Marina
Interior

Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN

Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
Bradenton
10.0 out of 10, Exceptional, (12 reviews)
"The place is cozy and conveniently located to IMG Academy. New appliances and very clean. There are chairs for the beach which is helpful; Coquina Beach is 20 mins away."
United States
Jen
The price is AED 478
AED 1,236 total
includes taxes & fees
18 May - 19 May
Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
Property grounds

Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches

Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
Bradenton
9.8 out of 10, Exceptional, (70 reviews)
"Excellent stay. Great place that was nice, clean and quiet. "
United States
David S.
The price is AED 493
AED 1,416 total
includes taxes & fees
16 May - 17 May
Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
Beach nearby, beach towels

Stunning Condo · Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins

Stunning Condo · Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins
Bradenton
9.8 out of 10, Exceptional, (120 reviews)
"Perfect spot and host "
United States
Dee B.
The price is AED 447
AED 1,145 total
includes taxes & fees
1 Jun - 2 Jun
Stunning Condo · Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins
TV

Casa Azul By the River

Casa Azul By the River
Bayou Oaks
9.6 out of 10, Exceptional, (77 reviews)
"Wonderful stay! Would definitely book again if in the Sarasota area."
United States
Jessica
Casa Azul By the River
On the beach, sun loungers, beach towels

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (85 reviews)
"Beautiful condo!! The owner was very responsive and attentive. We will definitely recommend this place to anyone!"
United States
Kay C.
The price is AED 727
AED 1,597 total
includes taxes & fees
20 May - 21 May
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Pool

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG

Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG
South Bradenton
The price is AED 735
AED 1,844 total
includes taxes & fees
19 May - 20 May
Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG
Smart TV

Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (113 reviews)
"The host (Sergey) was very welcoming and a pleasure to deal with as well as the staff at the Inn. The unit was centrally located and amenities at the unit were terrific and just what we wanted. The view of the ocean from the balcony was magnificent."
United States
Robert P.
The price is AED 945
AED 1,870 total
includes taxes & fees
27 May - 28 May
Sunset and beach view from your balcony Unit 403
Beach nearby, sun loungers, beach towels

Lavish 2BR Condo! Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins

Lavish 2BR Condo! Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins
Bradenton
10.0 out of 10, Exceptional, (128 reviews)
"Great place to stay"
United States
Tawnee H.
The price is AED 430
AED 1,096 total
includes taxes & fees
26 May - 27 May
Lavish 2BR Condo! Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins
Sun loungers, beach towels

Beautiful Condo · Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins

Beautiful Condo · Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
The price is AED 413
AED 1,103 total
includes taxes & fees
26 May - 27 May
Beautiful Condo · Two Pools & Hot Tubs · IMG 5 Mins · Anna Maria Island 15 Mins
Terrace/patio

Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (10 reviews)
"Great property and a great host! Easy and enjoyable stay. Will absolutely do again."
United States
Chris and Cecilia Z.
The price is AED 658
AED 1,983 total
includes taxes & fees
24 May - 25 May
Turtle Nest
Terrace/patio

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (58 reviews)
"Everything was great. "
United States
Maribel
The price is AED 279
AED 555 total
includes taxes & fees
15 Jun - 16 Jun
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Sun loungers

*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (61 reviews)
"Host was very responsive and provided helpful information for our stay."
United States
Azure G.
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Beach nearby

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Everything was great "
United States
kirt v.
The price is AED 675
AED 1,469 total
includes taxes & fees
6 Jun - 7 Jun
Best views of the beach from your balcony Unit 301
Beach nearby, sun loungers, beach towels, snorkeling

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Sarasota
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful location Perfect for what we wanted in a quick escape. "
United States
Antonio
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Sun loungers, beach towels

Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches

Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches
Bradenton
9.8 out of 10, Exceptional, (95 reviews)
"Very nice accommodations! I would suggest putting a shelf or niche in the master shower! There is only a soap dish with no where to sit shampoo, body wash etc!! Thank you for your kindness!! "
United States
Kimberly
The price is AED 441
AED 1,120 total
includes taxes & fees
7 Jun - 8 Jun
Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches
Interior

3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf

3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
Manasota Key
9.2 out of 10, Wonderful, (67 reviews)
"The host, Andrew, was very responsive. Answered all the questions, made sure the check in went smoothly, and provided all the necessary details ahead of time. The property is beautiful. Kitchen well stocked with dishes and utensils. We enjoyed cooking on the gas grill- Property even provides the propane. The sunset views were phenomenal."
United States
jenifer
The price is AED 727
AED 1,597 total
includes taxes & fees
18 May - 19 May
3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
On the beach, beach umbrellas

Gulf Views – Silver Sands #250, Longboat Key by RVA

Gulf Views – Silver Sands #250, Longboat Key by RVA
Longboat Key
9.0 out of 10, Wonderful, (77 reviews)
"The host staff were very helpful."
United States
Ann S.
The price is AED 790
AED 1,515 total
includes taxes & fees
18 May - 19 May
Gulf Views – Silver Sands #250, Longboat Key by RVA
Sun loungers, beach towels

Beautifully furnished condo

Beautifully furnished condo
Bradenton
9.8 out of 10, Exceptional, (157 reviews)
"We would stay there again."
United States
Connie S.
The price is AED 533
AED 1,158 total
includes taxes & fees
15 Jun - 16 Jun
Beautifully furnished condo
Exterior

Sandy Toes & Sun Kissed Nose: Open Monday & Tuesday, $203/nt + Fees!

Sandy Toes & Sun Kissed Nose: Open Monday & Tuesday, $203/nt + Fees!
Longboat Key
9.6 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, the condo was very well equipped and the host was absolutely fantastic! "
United States
Emily L.
The price is AED 744
AED 1,444 total
includes taxes & fees
18 May - 19 May
Sandy Toes & Sun Kissed Nose: Open Monday & Tuesday, $203/nt + Fees!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Clean room and bathroom, Kirstin was great with an early check in."
David 5-night trip
Posted 2 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from AED 555 to AED 2,125 per night. These stays provide loads of space for your whole crew at a price that's friendly on the pocket. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Osprey?
Choose from multiple condos in Osprey with a total average guest review rating of 9.7. Venice Beach Villas comes highly recommended if you're traveling with the whole crew or just want to stretch out. This 3-star condo also features therapeutic mineral springs and a barbecue grill. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another guest fave. It has a 3-star rating and amenities such as a deck and a lanai.
How many condos are there in Osprey?
Work out your vacation dates and then pick from 3715 condos in Osprey. For an official business trip, a couples' getaway or anything in between, Expedia will help you find the perfect place in a few quick clicks.
Are there any 5-star condos in Osprey?
Although there are no 5-star condos in Osprey, there are 4-star accommodations that have what you're looking for. Located about 11 kilometers from the downtown area, Gulf Holiday By Beachside Management comes with concierge services and a swimming pool. Another upscale retreat is Excelsior Beach To Bay - Bayside. It's roughly 8 kilometers from the center of Osprey and has amenities like a swimming pool and a deck.
Why book your condo in Osprey with Expedia?
With Expedia, it's a cinch to find your ideal condo in Osprey. After someplace luxurious? Make the most of our filters to search for properties that have a 5-star rating. If you have a set budget, select how much you're willing to spend and then browse our amazing options. We'll help you find the perfect fit whatever your escape looks like.
How can I find cheap condos in Osprey?
With Expedia's user-friendly filter tool, comparing cheap condos in Osprey is a snap. To discover properties that'll make your wallet happy, refine your search by amenities, budget and star rating.